Hello. How are you all? I recorded this interview with Ben Sinclair from High Maintenance a few weeks ago. 

Today, I’m recording in a makeshift studio in my back bedroom. We at Death, Sex & Money are talking a lot about how to be there with you while so much our what’s familiar is falling away. More on that later in the show. For now, just enjoy this conversation.

BEN SINCLAIR: Well, one thing that I have been kind of going into this press circuit with was hoping that I could distance myself from the divorced stoned guy persona that is well documented, but I am divorced and I do get stoned.

This is Death, Sex & Money. 

The show from WNYC about the things we think about a lot...

...and need to talk about more. 

I’m Anna Sale.

In HBO’s High Maintenance, Ben Sinclair plays a weed dealer in New York who bikes around the city, shows up at your doorstep, and then opens up his backpack to sell you what you want. 

UNIDENTIFIED WOMAN: “So, you’re a pot dealer, what’s that like?" 

BEN SINCLAIR IN HIGH MAINTENANCE: "Uh, I just kind of bike around and people call me, and I bring them weed.”

Ben’s character sees a lot—the show is much more about human relationships and eccentricities than using drugs. And I love it. The episodes feel like closely observed poems about everyday encounters in New York City. 

But Ben didn’t grow up in New York. He first arrived in the city about a year after college, in the summer of 2007. He came after getting an audition to join the Blue Man Group, but that didn’t go well.

BS: I remember feeling like a lot, my whole life was riding on this audition and my dad jumped the gun as he tends to and he was telling everybody that I was in Blue Man Group.

AS: Oh no. (Laughs)

BS: And thank God social media wasn't as popular as it is now because that would have been a disaster. But he bought me like a velvet blue thing in a thrift store that he found, like a suit. And then after that I walked around the Lower East Side. I went from bodega to bodega eating just trash. It was like this m, it was the, it was a bodega crawl of stress eating. 

AS: Like what were you eating?

BS: Oh one, I got a, I remember, a little bag of pizza-flavored Combos from a Duane Reade.

AS: Oh no. That’s bad.

BS: And then I went to across the street and I got a knish, a potato knish from somewhere and then a piece of pizza from somewhere else. I was freaking out. And then, uh, and then I just decided to stay in New York after that. I was like, well, I have to get something from this situation.

Ben couch surfed for a year while he threw himself into whatever acting opportunities he could find. Then he tried training to become a New York City public school teacher, but quickly dropped out of the program.

BS: And I was like, alright, no more teaching, no more paying rent. I found an internship, a theater internship on Craigslist that ended up allowing me to live in a, in the lobby of a theater, of a black box theater for about a year.

AS: You lived in a lobby in a theater in Midtown Manhattan for a year?

BS: Yes. Near Bellevue Hospital. The theater was run by a mime named Richmond Shepard, who, who was 80 something years old at the time. And he had bought this theater and filled it, uh he kind of made it a shrine to his mimery, I, I guess. There were pictures of him and Lily Tomlin in white face makeup from 1960.

AS: Oh.

BS: You know.

AS: Yeah.

BS: It was a real weird scene. Holy crap. And - 

AS: What did you sleep on?

BS:  I slept on a futon that I made him purchase off of Craigslist. And twice a week his ex wife would come in and sleep on a foam pad on the stage because she was a children's clown performer. And then she would try to do Reiki on me. And then, and then at night I would go to sleep and I slept right in front of like this grated window. And I would watch the shadows of rats crawl up this grating. So it all felt very, very, uh uh, necessary. And part of that romantic coming to New York story that I really wanted in my boring suburban life when I was young. Well, I got it. 

Ben grew up in the suburbs of Scottsdale, Arizona. His mom was a cantor at a local synagogue, his dad was a teacher. Ben was the youngest of their four kids. 

BS: I'm actually reading all of this kind of Jungian, Freudian unconscious stuff right now. And, uh, I, I feel like my status as the youngest of four really had a big part to do with my, the formation of my personality because there was a very overachiever, um, quality to the, the rearing of the children in my family. And uh you know, my older, eldest sister went to Yale, and then both my brothers went to Northwestern, and there was an emphasis on education. And as the youngest, you're like, oh, I gotta set my identity up. So the, as you go down the line of siblings, there are less safe ways to get attention. And then as you're trying to claim your identity, by the time you get to the fourth, you're like, alright, well, just don't do what the rest of them did, and act out a little bit differently. So I kind of cultivated, I don't—I didn't "kind of" cultivate anything. I definitely cultivated a personality, uh, that was trying to uh, get attention by positive or negative means. Uh, I just wanted attention.

AS: And and like how early did that start?

BS: Oh, bro. I I, I was, I would just be on like my little tricycle, and just pedal as fast as I could straight into the wall, just straight into the wall, just to get an, just to get a rise, just to see what would happen. Uh, and in the multitude of introspection that I've been doing for the past, you know, whatever, decades, I've, I've found that it, uh there was this pressure to be good uh always. And by pushing the boundaries of being good I used to get in a lot of trouble.

AS: And so for you, when you, like you, you would get attention by doing things that, that were uh, bad. Um, but like when you think about your relationship with your parents when you were a teenager for example, was it sort of like you were the lovable rebel or, or was it kind of like serious, um serious crossing the line that, that, that really stressed out the family? 

BS: I would call myself a functional rebel. I was very punctual and everything, but I was also experimenting with all sorts of drugs and ignoring curfews and uh taking advantage of my tired parents essentially who were dealing with, you know, my, my high school and middle school times were kind of taken up with focus on my father's health. Uh, he had some health issues spanning many years, uh, those years of my life. So at that point I kind of, mm arguably raised myself. Uh, and you know, I'm sure everybody at the time was like, oh this is, this is bad news. Like, you know, there was some vandalism happening, I remember, oy yoy yoy. We used to go out and, I guess this is unkind, but we used to take pots, like terra-cotta pots from people's front yards and then used to drive them to a little secluded ditch and just destroy them with bats. And only now am I reflecting on that as like a, a physical execution of internal suburban frustration. Yeah. I would describe being in the suburbs of uh, of Scottsdale, Arizona as a frustrating experience.

AS: Did you feel lonely as a kid? 

BS: Yes, definitely. Definitely. Yeah -

AS: Even like surrounded by siblings, they were in the house with you at the time when you're growing up?

BS: Yeah. Yeah. But, uh, so both of my parents came from military families. My parents met on a, Andrews Air Force Base when they were 12. Uh, and they've been together - 

AS: Twelve! Whoa. 

BS: I think my dad was 14, my mother was 12. And then they've been together since. 

AS: Wow.

BS: All of my siblings have, are with spouses that they met in college. I don't think anybody in my family has dated like, you know, outside of the structured education system. Uh, so, so uh, my family is pretty, I, like I only recently kind of—ugh, why do I say "kind of?"—I only recently took into stock that the military background that my, that affected my family has a lot to do with us repressing things and just doing the "right thing" and having a very conditional, "if you do this then this will happen, and you, all you have to do is go to college." And you know fitting life into neat little boxes and achievements.

AS: Yeah, a real faith in rules. 

BS: A faith in rules.

Coming up, Ben talks about his marriage...and divorce...from Katja Blichfeld, whom he co-created High Maintenance with.

BS: I don't know at the time that either of us could conceive of a creative relationship between two people who also found each other attractive as just being a creative relationship. I think we had to do the whole kit and caboodle.

—

Hello—it’s Anna, recording from the closet again. As we adjust to this new, physically distanced reality, we are releasing more frequent newsletters. So if you’re not a subscriber, go to deathsexmoney.org/newsletter, and get in on that. 

So far this week, we’ve sent out a few newsletters that include updates from you about what you’re thinking about and how your lives have changed. You’re also telling us how you’re being there for others. 

We started that conversation last week with a live call-in that I hosted with Kai Wright from the podcast The United States of Anxiety. If you missed it, it’s in your feed right now. It was great to talk with some of you who are facing real sudden change and uncertainty—Maddie cancelled her wedding, Tierra is worried about her dorm housing and work-study job, Dale lives alone and worries about isolation for seniors like her. We shared tips for staying connected in this time of distancing, and chef Samin Nosrat gave us the hot tip to use this time to start an herb garden to add a little freshness for our pantry-based meals at home. 

We’re thinking about the best way to be with you in this wild, unprecedented times. One way is we want to talk to you all more. So send us an email at deathsexmoney@wnyc.org if you want to have a phone chat—and tell us what you want to talk about. 

And our next episode? We’re still figuring that out right now. But watch your feed and your email inbox. We’re going to be with you through the duration. 

—

This is Death, Sex & Money from WNYC. I’m Anna Sale. 

Right before Ben Sinclair turned 25, he went to visit his brother in LA. It was on that trip that he met Katja Blichfeld...who was six years older than him, and working in casting for TV shows. 

BS: Basically my brother and sister-in-law were friendly with Katja and they were trying to set her up with another friend of theirs. And then I showed up at the party and it was clearly on between her and I. Uh, I think if I hadn't been so, like, living from hand to mouth, and feeling very scrappy and kind of scared, honestly.

AS: Uh huh. Yeah.

BS: I didn't have, uh, any safety net. I was really flying without a net at that time of my life. And this was a person who had been working on, you know, a working professional with like a real job with, who I was like, wow, you're, you're, you've got, clearly got good tastes, but also you're a functional stoner like I am. And also like, it's very easy to talk to you. And very soon after I met her, all of that, that fear that I was feeling was absorbed by her care and I felt safe again. So I think that safety that I felt with her and the recognition that my life had never felt as good as this before her made the decision to marry her very easy for me.

AS: Yeah. I mean, it sounds like you had found a way to have the kind of structure that you knew from growing up, but, but on your terms in a way?

BS: Yes.

AS: That like, yeah.

BS: Exactly. 

AS: That must've felt amazing. 

BS: It did.

AS: Who’s idea was it to get married?

BS: We were in bed, uh, I brought up the notion that of, of, well I don't think I would, can imagine marrying anybody else. Like, I can't imagine being with anybody else. And then she said, well, does that mean you want to get married? And I was like, well, are, are you asking me to do that? And she goes, yes I think I am asking you to do that. And I said, well, well yes. And we were both very stoned at the time. We were actually recording ourselves—we had a flip cam at the time and we were using the flip cam all the time to document our romance.

AS: Whoa. 

BS: Uh, and if I watch the video from the day after that ask, and I have watched it before, it's kinda hard to watch because you can see me be like, wait what did we just do? 

AS: What do you notice?

BS: Mm. I have shifty eyes and I'm looking down a lot. Um, I think I was like, oh, okay. Okay. Okay. Okay.

AS: Did you rewatch that after your marriage ended or when did you last watch that?

BS: Mmhm. I’ve watched it, I watched it, I don't know, a couple of years ago, but also at the time when we filmed it, like, you know, I felt, I felt weird. I felt -

AS: Uh huh.

BS: That I had made a decision stoned. Uh, and then I was sober the next day and reviewed that decision. Uh, and I continued the process because I still felt like it was the right and good thing to do. I hadn't had the respect from my family that I had until I met Katja and brought her home and all of the siblings all of a sudden had their spouses and, or their, their significant others. And there was a feeling of acceptance. I felt like I was finally uh meeting the expectations that were had of me. 

Ben and Katja came up with the idea for High Maintenance together. They started making it as a web series in 2010, the same year they got married. The show grew a following online, and in 2015, HBO picked it up.

But as the couple’s success grew, their marriage suffered. Katja eventually came out as a lesbian. They separated in 2016.

BS: I think we both noticed, uh, early on some things that we both repressed, swept under the rug. So I think we carried in each of us for many years, a feeling that something was off. But you know what, life hasn't been as good as it is, has ever been up to now. And that com, got compounded when we started receiving a lot of accolade for our, our little art project. It felt like to give up this thing that we had always felt a little that was missing one very key ingredient was we just needed to suck it up, and just let all of these good things that were happening to us just continue. 

AS: Like it was a trade off. Like it was part of the pressure, just part of what was, it was a trade off to have what you had, built together.

BS: Yes. It was just like a feeling within us, that was like - you could convince yourself that's just a feeling and, uh, it's just a feeling. Uh, and if you tell yourself the story enough that like, "Oh, I have feelings and this is just a part of an anxious personality. This is just part of, uh, who I am." But the truth is like, there are some things, the, clearly there was something going on for her that was much larger than just her and I, it was an identity thing. And clearly there was, uh, a feeling of me feeling unsafe that I didn't want to return to. I didn't trust that I could take care of myself, you know? I don't think I, I don't think I got the - the confidence that I could be an adult male that people weren't worried about. And I still struggle with not engaging in dependency. But man, I am very stuck on the notion that just because something ends doesn't mean it's a failure. Uh, and I think it's, there's this very unfair expectation on marriage that it lasts forever. I think that's so dumb. Um, so many good things end. Great movies end, seasons end. Like what I'm noticing is the, the, the pain of a lot of my friends who are getting divorced is like, "Oh man, I messed it up. I didn't, it didn't work out, and I'm bad and, and I, there must be something wrong with me because I couldn't make it work forever." I guess you have to go through it and you have to come to that realization on your own. But I really am a fan of, of things ending now.

AS: When you were first, uh, living back on your own, did you, did you move out and move into a place by yourself when your marriage was over? 

BS: No. Well, we were sharing this huge apartment that we were able to land. It was like a, no joke, 2000 square foot apartment. 

AS: Wow.

BS: And I, we made a deal that, uh, I would sublet some places and then come back at a certain date. It felt, it was hard, man. Whoa. That's probably the hardest time of my life was the, the fresh breakup, but then going to work with each other every day. And then - 

AS: And not having a place to land that was permanent.

BS:  Yes. And then living in some strange place. That might've been the hardest time of my life. And then, uh, after a couple of seasons on High Maintenance, I had accrued enough money to buy a place. So I've bought a place, a one bedroom that, and it's the first time I've ever lived alone in my entire life. Ever, ever. Have, have you ever lived alone? 

AS: Well, I was living alone, I, the first time I ever lived alone, I was divorced, and in New York City, and I was stunned to realize that I'd never lived alone before. It’s like - 

BS: Most people don't. 

AS: Yeah.

BS: It's, I mean, a lot of people do, but a lot of people—a lot, a lot, a lot of people—no one in my family has really lived alone for a long time.

AS: Was it unsettling to you at all to be alone? 

BS: Yes. Loneliness is my greatest fear for sure. No doubt. It is definitely my greatest fear. Um, and coming to terms with being alone was huge.

AS: When you mentioned that you, you like, you wanted to, to project a version of yourself that wasn't the divorced weed guy, um, like what feels, what feels ill-fitting about that caricature now for you?

BS: There's just so much more to it. I, I, I feel like, uh, that the weed part, it, you would think it would be different, but people, it's still such a turnoff to so many people. But I have noticed lately that I'm starting to grow out of smoking weed. Uh, I'm starting to not feel relief when I'm stoned. It's more that I feel joy at the anticipation of getting stoned, but once I'm stoned, I'm like, ugh, why did I do this? And that has been a big thing for me lately of like understanding that addiction is continued use despite adverse results. Uh, making that connection has been very helpful to me because I can be stoned and be like, I don't want to be stoned right now, so why am I still getting stoned? And identifying that it's the anticipation, that Pavlovian bell ringing that's really, that I'm, I'm really after. It's the bell, not the treat. 

AS: Mmhm.

BS: And, uh, and maybe Anna, maybe it's because I don't want to seem weak. Maybe it's because I don't want to seem like a person who's dulling their pain uh with a substance. I don't know if that's it. I'm, it's probably a male wish to not appear weak at the end of the day. But I feel weakness. And I would rather be a person who is working on uh joy then numbing of pain. I would like to be associated with joy. 

That’s Ben Sinclair. You can watch High Maintenance on HBO. I love many, many of their episodes. There’s a list of my top five in our show notes. 

Death, Sex & Money is a listener-supported production of WNYC Studios in New York. I’m based at the studios of the investigative podcast Reveal in Emeryville, California. Our team includes Katie Bishop, Anabel Bacon, Afi Yellow-Duke, Emily Botein, and Andrew Dunn.

Our intern is Ayo Osobamiro. 

The Reverend John Delore and Steve Lewis wrote our theme music. 

And thanks to Nancy Bergstrom in Burr Rudge, Illinois, who’s a sustaining member of Death, Sex & Money. Join Nancy and support what we do here by going to deathsexmoney.org/donate.

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AS: Are you replacing weed with something else?

BS: Believe it or not? I've been drinking more. Can you believe it? I can. Uh, yeah, I've like, I've, I've, I don't drink by myself ever. Uh, but I, one night I did and I'm like, whoa, look at that. Look at you, look at you being all Don Draper and shit. 

AS: What did you drink? 

BS: Tequila. A glass of tequila. Weird.

I’m Anna Sale, and this is Death, Sex & Money from WNYC.